Organic electrical components, organic electrical components using the same compounds, and electronic devices thereof.

Abstract

The present invention provides an organic electrical element comprising a compound represented by chemical formula 1, including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, and an electronic device comprising the organic electrical element, wherein the organic layer comprises a compound represented by chemical formula 1, thereby enabling a reduction in the driving voltage of the organic electrical element and an improvement in the luminous efficiency and lifespan of the organic electrical element.

Description

Technical Field

[0001] This invention relates to compounds for organic electrical components, organic electrical components utilizing the same, and electronic devices thereof. Technical Field

[0003] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical components utilizing organic light emission usually have an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of the organic electrical components, the organic layer is generally formed as a multilayer structure composed of various materials; for example, it can be formed as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0004] In organic light-emitting diodes (OLEDs), the most problematic aspects are lifespan and efficiency. As displays become increasingly larger, these efficiency or lifespan issues have become matters that must be addressed.

[0005] Efficiency, lifespan, and driving voltage are interrelated. If efficiency increases, the driving voltage decreases relatively. When the driving voltage is reduced and the driving is engaged, the crystallization of organic materials based on Joule heating decreases, ultimately leading to a tendency for increased lifespan.

[0006] However, even simply improving the aforementioned organic layers cannot maximize efficiency. This is because long lifespan and high efficiency can only be achieved when the energy levels and T1 values ​​of each organic layer, as well as the inherent properties of the materials (mobility, surface properties, etc.), are optimally combined.

[0007] Furthermore, in recent years, in order to solve the problem of light emission in the hole transport layer for organic light-emitting elements, a light-emitting auxiliary layer must exist between the hole transport layer and the light-emitting layer. Different light-emitting auxiliary layers need to be developed for each light-emitting layer (R, G, B). Summary of the Invention

[0008] Technical issues

[0009] The object of the present invention is to provide compounds that can reduce the driving voltage of components and improve luminous efficiency and lifespan, and organic electrical components and electronic devices utilizing the same.

[0010] Technical solution

[0011] In one aspect, the present invention provides compounds represented by the following chemical formula.

[0012]

[0013] In another aspect, the present invention provides an organic electrical component and electronic device thereof utilizing a compound represented by the above chemical formula.

[0014] Technical effect

[0015] By utilizing the compounds of the present invention, not only can the driving voltage of the device be reduced, but the luminous efficiency and lifespan of the device can also be improved. Attached Figure Description

[0016] Figures 1 to 3 This is an example diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0017] Explanation of reference numerals in the attached figures

[0018] 100, 200, 300: Organic electrical components; 110: First electrode

[0019] 120: Hole injection layer; 130: Hole transport layer

[0020] 140: Light-emitting layer; 150: Electron transport layer

[0021] 160: Electron injection layer; 170: Second electrode

[0022] 180: Light efficiency improvement layer; 210: Buffer layer

[0023] 220: Light-emitting auxiliary layer; 320: First hole injection layer

[0024] 330: First hole transport layer; 340: First luminescent layer

[0025] 350: First electron transport layer; 360: First charge generation layer

[0026] 361: Second charge generation layer; 420: Second hole injection layer

[0027] 430: Second hole transport layer; 440: Second luminescent layer

[0028] 450: Second electron transport layer; CGL: Charge generation layer

[0029] ST1: First stack ST2: Second stack Detailed Implementation

[0030] In this invention, the terms "aryl" and "arylene" as used herein, unless otherwise specified, refer to compounds having a number of carbons from 6 to 60, but are not limited thereto. In this invention, aryl or arylene compounds include monocyclic, cyclic aggregates, fused polycyclic, and spirocyclic compounds, etc. Furthermore, unless explicitly stated in this specification, aryl may contain fluorene, and arylene may contain fluorene.

[0031] In this invention, the term "fluorenyl" means substituted or unsubstituted fluorenyl, and "fluoreneyl" means substituted or unsubstituted fluoreneyl. Fluorenyl or fluoreneyl compounds as used in this invention include spiro compounds formed by the interaction of R and R' in the following structures, and also include cyclic compounds formed by the interaction of adjacent R" groups. "Substituted fluorenyl" and "substituted fluoreneyl" mean that in the following structures, at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R" in the following structures can be 1 to 8 valences. Regardless of valence, fluorenyl, fluoreneyl, and fluorenetrimethyl groups may all be referred to as fluorenyl in this specification.

[0032]

[0033] In this invention, the term "spirocyclic compound" means "spiro union," which implies a connection achieved by two rings sharing only one atom. The atom shared between the two rings is called a "spirocyclic atom," and these are referred to as "monospirocyclic," "bispirral," and "trispirral" compounds, respectively, depending on the number of spirocyclic atoms contained in the compound.

[0034] The term "heterocyclic group" as used in this invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene," but also non-aromatic rings. Unless otherwise specified, it means a ring with 2 to 60 carbon atoms containing one or more heteroatoms, but the invention is not limited thereto. The term "heteroatom" as used in this invention, unless otherwise specified, refers to elements other than carbon, such as N, O, S, P, or Si, and may also include compounds containing heteroatomic groups such as SO2, P=O, etc., instead of the carbon forming the ring. Heterocyclic group means monocyclic, cyclic aggregates, fused polycyclic, and spirocyclic compounds containing heteroatoms.

[0035]

[0036] The term "aliphatic cyclic group" as used in this invention means cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic, cyclic aggregates, fused polycyclic and spirocyclic compounds, etc. Unless otherwise specified, it means a ring with 3 to 60 carbon atoms, but is not limited thereto. For example, the fusion of benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, also corresponds to an aliphatic ring.

[0037] In this specification, the "group name" corresponding to aryl, arylene, heterocyclic, etc., shown by way of examples of various symbols and their substituents, may be written as "the name of the group reflecting the valence," but it may also be written as "the name of the parent compound." For example, in the case of "phenanthrene," which is an aryl group, the monovalent "group" is "phenanthrene(yl)," the divalent group is "epenphenanthrene(yl)," etc. The name of the group may be written by distinguishing the valence, but it may also be written as "phenanthrene" as the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it may be written as "pyrimidine," regardless of the valence, or it may be written as "the name of the group with that valence," for example, in the case of monovalent, it may be written as pyrimidinyl, and in the case of divalent, it may be written as pyrimidinyl, etc.

[0038] Furthermore, when describing the names of compounds or substituents in this invention, numbers or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofurano[2,3-d]pyrimidine as benzofuranopyrimidine, and 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzo[g]quinoxaline.

[0039] Furthermore, unless otherwise specified, the chemical formulas used in this specification are applicable in the same way as the definitions of substituents defined by the index of the following chemical formulas.

[0040]

[0041] Where, when a is an integer of 0, the substituent R 1 If a is 0, it means that all carbons forming the benzene ring are bonded to hydrogen. In this case, the representation of the hydrogens bonded to the carbons can be omitted, and the chemical formula or compound can be written. Furthermore, if a is an integer of 1, a substituent R... 1 It combines with one of the carbons used to form the benzene ring, in the following manner when a is an integer of 2 or 3, and in a similar manner with the carbons of the benzene ring when a is an integer from 4 to 6, and R when a is an integer greater than 2. 1 They can be the same or different from each other.

[0042]

[0043] Furthermore, unless otherwise stated in this specification, when representing condensed rings, the number in 'numerical-condensed ring' indicates the number of condensed rings. For example, the condensed form of three rings such as anthracene, phenanthrene, and benzoquinazoline can be represented as a 3-condensed ring.

[0044] Furthermore, unless otherwise stated in this specification, when a ring is represented in the form of 'numerical atom' such as a five-membered ring or a six-membered ring, the number in 'numerical-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.

[0045] Furthermore, unless otherwise stated in this specification, the rings formed by the bonding of adjacent groups are selected from C6 to C6. 60 Aromatic cyclic groups; fluorene groups; C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0046] In this specification, unless otherwise stated, 'between adjacent groups' means, taking the following chemical formulas as examples, not only between R1 and R2, R2 and R3, R3 and R4, and R5 and R6, but also between R7 and R8 sharing a carbon atom. It can also include substituents bonded to non-directly adjacent ring-forming elements (carbon or nitrogen, etc.), such as between R1 and R7, R1 and R8, or R4 and R5. That is, when a ring-forming element such as directly adjacent carbon or nitrogen has a substituent, it can be considered an adjacent group. However, when no substituent is bonded to a ring-forming element in a directly adjacent position, it can be considered an adjacent group with a substituent bonded to the next ring-forming element. Furthermore, substituents bonded to the same ring-forming carbon atom can also be called adjacent groups.

[0047] In the following chemical formulas, when substituents such as R7 and R8 bonded to the same carbon atom to form a ring, a compound containing a spirocyclic moiety can be formed.

[0048]

[0049] Furthermore, the expression 'adjacent groups can combine to form a ring' in this specification is used to mean the same thing as 'adjacent groups can combine to selectively form a ring', and implies the situation where at least one pair of adjacent groups combine to form a ring.

[0050] Below, refer to Figures 1 to 3 The layered structure of organic electrical components containing the compounds of the present invention will be described.

[0051] When affixing reference numerals to the structural elements in the accompanying drawings, care should be taken to assign the same reference numerals to the same structural elements, even if they are shown in different drawings. Furthermore, in describing the invention, detailed descriptions will be omitted where it is determined that a detailed explanation of a known structure or function would obscure the essence of the invention.

[0052] In describing the structural elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are used only to distinguish the structural elements from each other, and the nature, order, or sequence of the related structural elements are not limited by these terms. When a structural element is "connected," "combined," or "linked" to another structural element, the structural element may be directly connected or linked to the other structural element, but it can also be understood that other structural elements are "connected," "combined," or "linked" between the structural elements.

[0053] Furthermore, when structural elements such as layers, membranes, regions, and plates are located "above" or "above" other structural elements, this can be understood not only as being "directly above" other structural elements, but also as having other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood as having no other part in between.

[0054] Figures 1 to 3 This is an example diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0055] Reference Figure 1 An embodiment of the organic electrical component 100 of the present invention includes: a first electrode 110 formed on a substrate (not shown), a second electrode 170, and an organic layer between the first electrode 120 and the second electrode 170. The first electrode 120 can be an anode, and the second electrode 170 can be a cathode. In the inverted type, the first electrode can be a cathode and the second electrode can be an anode.

[0056] The aforementioned organic layer may include a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, the hole injection layer 120, the hole transport layer 130, the light-emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be formed sequentially on the first electrode 110.

[0057] Preferably, a light efficiency improvement layer 180 can be formed on one of the two sides of the first electrode 110 or the second electrode 170 that does not contact the organic layer. When the light efficiency improvement layer 180 is formed, the light efficiency of the organic electrical component can be improved.

[0058] For example, a light efficiency improvement layer 180 can be formed on the second electrode 170. However, in the case of a top-emission organic light-emitting diode, the formation of the light efficiency improvement layer 180 can reduce the optical energy loss caused by surface plasmon polarizations (SPPs) in the second electrode 170. In the case of a bottom-emission organic light-emitting diode, the light efficiency improvement layer 180 can perform a buffering effect on the second electrode 170.

[0059] A buffer layer or a light-emitting auxiliary layer may also be formed between the hole transport layer 130 and the light-emitting layer 140. For this purpose, refer to... Figure 2 Please provide an explanation.

[0060] Reference Figure 2 According to another embodiment of the present invention, the organic electrical component 200 may include a hole injection layer 120, a hole transport layer 130, a buffer layer 210, a light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 formed sequentially on a first electrode 110, and a light efficiency improvement layer 180 may be formed on the second electrode.

[0061] Although not illustrated Figure 2 An electron transport auxiliary layer may also be formed between the light-emitting layer 140 and the electron transport layer 150.

[0062] Furthermore, according to another embodiment of the present invention, the organic layer may also be in the form of a stack comprising multiple hole transport layers, light-emitting layers, and electron transport layers. See also... Figure 3 Please provide an explanation.

[0063] Reference Figure 3 According to another embodiment of the present invention, the organic electrical element 300 may form two or more stacks (ST1, ST2) of organic layers arranged in multiple layers between the first electrode 110 and the second electrode 170, and a charge generation layer CGL is formed between the stacks of organic layers.

[0064] Specifically, an organic electrical component according to an embodiment of the present invention may include a first electrode 110, a first stack ST1, a charge generation layer CGL (charge generation layer), a second stack ST2, a second electrode 170, and a light efficiency improvement layer 180.

[0065] The first stack ST1, as an organic layer formed on the first electrode 110, may include a first hole injection layer 320, a first hole transport layer 330, a first light-emitting layer 340, and a first electron transport layer 350. The second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second light-emitting layer 440, and a second electron transport layer 450. Thus, the first and second stacks may be organic layers with the same stacked structure, or they may be organic layers with different stacked structures.

[0066] A charge generation layer CGL can be formed between the first stack ST1 and the second stack ST2. The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361. This charge generation layer CGL, formed between the first light-emitting layer 340 and the second light-emitting layer 440, increases the current efficiency generated in each light-emitting layer and plays a role in smoothly distributing charge.

[0067] Although the first light-emitting layer 340 may include a light-emitting material containing a blue fluorescent dopant in a blue body, and the second light-emitting layer 440 may include a material containing a green body doped with both greenish yellow and red dopant, the materials of the first light-emitting layer 340 and the second light-emitting layer 440 according to embodiments of the present invention are not limited thereto.

[0068] exist Figure 3 In this case, n can be an integer from 1 to 5, but when n is 2, a charge generation layer CGL and a third stack can be further stacked on the second stack ST2.

[0069] like Figure 3 By forming multiple light-emitting layers through a multi-layer stacked structure, it is possible not only to fabricate organic electroluminescent elements that emit white light by means of the mixing effect of light emitted from each light-emitting layer, but also to fabricate organic electroluminescent elements that emit light of multiple colors.

[0070] While the compound represented by Chemical Formula 1 of the present invention can be used as a material for hole injection layers 120, 320, 420, hole transport layers 130, 330, 430, buffer layer 210, light-emitting auxiliary layer 220, electron transport layers 150, 350, 450, electron injection layer 160, light-emitting layer 140, 340, 440, or light efficiency improvement layer 180, it is preferred to use it as a material for light-emitting auxiliary layer 220.

[0071] Even with the same or similar nuclei, the band gap, electrical properties, and surface properties may differ depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the nucleus and the combination of its bonded substituents. In particular, when the energy levels and T1 values ​​between the organic layers, as well as the inherent properties of the material (mobility, surface properties, etc.) are optimally combined, long lifetime and high efficiency can be achieved simultaneously.

[0072] Therefore, the compound represented by chemical formula 1 in this invention is used as the material of the light-emitting auxiliary layer 220, thereby optimizing the energy level and T1 value, inherent characteristics (mobility, surface characteristics, etc.) between organic layers, while improving the lifespan and efficiency of organic electrical components.

[0073] An organic electroluminescent element according to an embodiment of the present invention can be fabricated using various vapor deposition methods. It can be fabricated using vapor deposition methods such as PVD or CVD. For example, it can be fabricated by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate to form an anode 110, and then forming an organic layer thereon including a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, an electron transport layer 150, and an electron injection layer 160, followed by depositing a material that can serve as a cathode 170 thereon. Furthermore, a light-emitting auxiliary layer 220 can be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) can be formed between the light-emitting layer 140 and the electron transport layer 150. As described above, it can also be formed in a stacked structure.

[0074] Furthermore, the organic layer utilizes various polymer materials and is formed into a smaller number of layers through solvent treatment or solvent refining methods other than vapor deposition, such as spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll coating, doctor blade coating, screen printing, or thermal transfer. Since the organic layer of this invention can be formed by various methods, the scope of protection of this invention is not limited by the formation method.

[0075] According to one embodiment of the present invention, the organic electrical component can be classified into front-emitting type, rear-emitting type or double-sided-emitting type based on the material used.

[0076] Furthermore, according to an embodiment of the present invention, the organic electrical component is selected from the group consisting of organic light-emitting elements, organic solar cells, organic photosensitive elements, organic transistors, monochrome lighting elements, and quantum dot display elements.

[0077] Another embodiment of the present invention may include an electronic device, which includes: a display device comprising the organic electrical components of the present invention described above; and a control unit for controlling the display device. In this case, the electronic device can be a current or future wireless communication terminal, and includes mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigators, game consoles, various TVs, various computers, and all other electronic devices.

[0078] Hereinafter, a compound of one aspect of the present invention will be described.

[0079] The compounds of one aspect of the present invention are represented by the following chemical formula 1.

[0080] <Chemical Formula 1>

[0081]

[0082] In the above chemical formula 1, each symbol can be defined in the following manner.

[0083] Ar 1 It has the following chemical formula A-1 or chemical formula A-2.

[0084]

[0085] Ar 2 and Ar 3 Choose independently from C6 to C6. 60 aryl; fluorene; C2-C containing at least one heteroatom selected from O, N, S, Si and P 60 Heterocyclic groups; and C3~C 60 It is a group composed of aliphatic rings.

[0086] X 1 It is O or S, and X 2 For N(R'), O or S,

[0087] R 1 To R 7 The groups are independently selected from hydrogen, deuterium, halogen, cyano, nitro, and C6–C. 60 aryl; fluorene; C2-C containing at least one heteroatom selected from O, N, S, Si and P 60 Heterocyclic groups; C3~C 60 Aliphatic cyclic groups; C1~C 30 Alkyl groups; C2-C 30 alkenyl group; C2~C 30 alkynyl group; C1~C 30 alkoxy groups; and C6~C 30 It is a group composed of aryl groups, and adjacent groups can combine with each other to form a ring.

[0088] a, c, d, e, f, and g are integers from 0 to 4, and b, e', and g' are integers from 0 to 3. Furthermore, when these are integers of 2 or higher, R... 1 R respectively 2 R respectively 3 R respectively 4 R respectively 5 R respectively 6 R respectively 7 They are the same or different.

[0089] Adjacent R 1 Between, adjacent R 2 Between, adjacent R 3 Between, adjacent R 4 Between, adjacent R 5 Between, adjacent R 6 Between, adjacent R 7 The ring formed by at least one pair of elements between them can be freely selected from C6 to C6. 60 Aromatic cyclic group; fluorene group; C2-C2 group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0090] When adjacent groups combine to form an aromatic ring, a C6-C6 ring can be formed. 30 C6~C 20 C6~C 16 C6~C 14 C6~C 10 Aromatic rings such as C6 can specifically form aromatic rings such as benzene, naphthalene, and phenanthrene.

[0091] When the ring formed by the combination of adjacent groups is a heterocyclic group, the aforementioned heterocyclic group can be, for example, C2 to C4. 30 C3~C 30 C4~C 30 C4~C 25 C4~C 24 C4~C 20 C4~C 18 C4~C 16 C4~C 12 C4~C 11 C4~C 10 , C4~C9, C4~C8, C4~C7, C4~C6, C4~C5, C4, C5, C6, C7, C8, C9, C 10 C 12C 16 Heterocyclic groups, specifically, can be heterocycles such as furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, etc.

[0092] illustratively, when adjacent R 3 When these molecules combine to form rings, the phenylene compounds bonded to them, together with the phenylene groups, can form compounds represented by the following chemical formula. That is, adjacent R... 3 They combine with each other to form 2-condensation rings such as benzothiophene and benzofuran, which can eventually form 3-condensation rings such as dibenzothiophene or dibenzofuran.

[0093]

[0094] Here, V 1 and V 2 It is defined as being identical to the definitions in Chemical Formulas 1-7 to 1-18 below.

[0095] L 1 To L 4 Independently selectable single bonds; C6~C 60 arylene; fluorene; C3~C 60 Aliphatic cyclic groups; and C2-C2 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 The group is composed of heterocyclic groups.

[0096] The above R' is selected from C6 to C6. 60 aryl; fluorene; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P. 60 Heterocyclic groups; and C3~C 60 The group is composed of aliphatic cyclic groups.

[0097] In the aforementioned Ar 2 Ar 3 R 1 To R 7 If at least one of R' is an aryl group, the aforementioned aryl group can be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C 21 C6~C 20 C6~C 19 C6~C 18C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 The aryl group can be benzene, biphenyl, naphthalene, terphenyl, phenanthrene, benzo[a]phenanthrene, etc.

[0098] In the above L 1 To L 4 When at least one of them is an arylene, the aforementioned arylene can be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C 21 C6~C 20 C6~C 19 C6~C 18 C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 The arylene group can be benzene, biphenyl, naphthalene, terphenyl, phenanthrene, etc.

[0099] In the aforementioned Ar 2 Ar 3 R 1 To R 7,R',L 1 To L 4 When at least one of them is a heterocyclic group, the aforementioned heterocyclic group can be, for example, C2 to C3. 30 C2~C 29 C2~C 28 C2~C 27 C2~C 26 C2~C 25 C2~C 24 C2~C 23 C2~C 22 C2~C 21 C2~C 20 C2~C 19 C2~C 18 C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 C 19 C 20 C 21 C 22 C 23 C 24 C 25 C 26 C 27 C 28 C 29Heterocyclic groups, specifically, can be pyridine, pyrazine, pyridazine, triazine, furan, pyrrole, thiorrole, indole, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazindoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthrenequinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, phenanthrenebenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenanthrenebenzothiophene, dinaphthothiophene, carbazole, benzene-carbazole, benzocarbazole, benzene-benzocarbazole Naphthalene-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuran-pyridine, benzothiophene-pyridine, benzofuran-pyridine, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiophene-pyrazine, benzofuran-pyrazine, benzimidazole, benzothiazole, benzoxazole, benzothirol, phenanthroline, dihydro-phenphenazine, 10-benzyl-10H-phenoxazine, phenoxazine, phenthiazine, dibenzodioxane, benzodioxane, thiazoline, 9,9-dimethyl-9H-xanthon, 9,9-dimethyl-9H-thiazoline, dihydrodimethylphenylacidine, spiro[fluorene-9,9'-xanthon], etc.

[0100] In the aforementioned Ar 2 Ar 3 R 1 To R 7 At least one of R' is fluorene or L 1 To L 4 When at least one of them is a fluorene group, the aforementioned fluorene group or fluorene group can be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirodifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthyl-2-yl)9-phenyl-9H-fluorene, etc.

[0101] In the aforementioned Ar 2 Ar 3 R 1 To R 7 ,R',L 1 To L 4 When at least one of them is an aliphatic cyclic group, the aforementioned aliphatic cyclic group can be, for example, C6 to C6. 30 C6~C 29 C6~C 28 C6~C 27 C6~C 26 C6~C 25 C6~C 24 C6~C 23 C6~C 22 C6~C21 C6~C 20 C6~C 19 C6~C 18 C6~C 17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aliphatic cyclic groups, etc.

[0102] The rings formed by the combination of the above-mentioned aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, and adjacent groups can be selected from deuterium, halogen, C1-C2, etc. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic groups, and C3~C 20 One or more substituents in the group consisting of aliphatic cyclic groups are further substituted.

[0103] When at least one of the rings formed by the combination of the above-mentioned aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups is further substituted by an aryl group, the aryl group may be, for example, C6 to C4. 20 C6~C 19 C6~C 18 C6~C17 C6~C 16 C6~C 15 C6~C 14 C6~C 13 C6~C 12 C6~C 11 C6~C 10 C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aryl groups, etc.

[0104] When at least one of the rings formed by the combination of the above-mentioned aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups is further substituted by a heterocyclic group, the above-mentioned heterocyclic group can be, for example, C2 to C4. 20 C2~C 19 C2~C 18 C2~C 17 C2~C 16 C2~C 15 C2~C 14 C2~C 13 C2~C 12 C2~C 11 C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 C 11 C 12 C 13 C 14 C 15 C 16 C 17 C 18 C 19 C 20 Heterocyclic groups such as...

[0105] When at least one of the rings formed by the combination of the above-mentioned aryl, arylene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, and adjacent groups is further substituted by an aliphatic cyclic group, the above-mentioned aliphatic cyclic group may be, for example, C3 to C4. 20 C3~C 19 C3~C 18 C3~C17 C3~C 16 C3~C 15 C3~C 14 C3~C 13 C3~C 12 C3~C 11 C6~C 10 C3~C6, C6, C 10 C 12 C 13 C 14 C 15 C 16 C 17 C 18 Aliphatic cyclic groups, etc.

[0106] When at least one of the rings formed by the combination of the above-mentioned aryl, aryl, fluorene, fluorene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkoxy, aryloxy, and adjacent groups is further substituted with a fluorene group, the fluorene group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirodifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphth-2-yl)9-phenyl-9H-fluorene, etc.

[0107] The above chemical formula 1 can be represented by one of the following chemical formulas 1-1 to 1-18.

[0108]

[0109]

[0110]

[0111] In the above chemical formulas 1-1 to 1-18, X 1 X 2 L 1 ~L 4 Ar 2 Ar 3 R 1 ~R 7 a to g are defined in the same way as in chemical formula 1, and e' and g' are integers from 0 to 3 respectively.

[0112] V 1 and V 2 They are mutually independent of each other as single bonds, O, S, C(R1)(R2) or N(R3), and V 1 and V 2 Except for cases where all keys are single keys.

[0113] R1 and R2 are independently selected from hydrogen, deuterium, halogen, and C1-C2. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic groups, and C3~C 20 It is a group composed of aliphatic ring groups, and adjacent R1 and R2 can combine with each other to form a ring.

[0114] R3 above is selected from C6 to C6. 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic group, C3~C 20 Aliphatic cyclic groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C1-C 20 Alkyl groups, C2-C 20 alkenyl groups, and C2-C 20 The group is composed of acetyl groups.

[0115] In the above chemical formula, Ar 2 and Ar 3 At least one of them can be selected from the group consisting of chemical formulas 2-1 to 2-6.

[0116]

[0117]

[0118] In the above chemical formulas 2-1 to 2-6, each symbol can be defined in the following manner.

[0119] X 4 and X 5 They are independently O, S, C(R1)(R2) or N(R3).

[0120] The above R1, R2, R 8 R 9 and R 10 Independently selected from hydrogen, deuterium, halogens, and C1 to C2 atoms. 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted silyl groups, C1-C 20 Alkyl or C6-C 20 aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C1-C6 groups 20 alkylthio groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C6-C 20 arylthiols, C1-C 20 Alkyl groups, C2-C 20 alkenyl, C2~C 20 alkynyl group, C6-C 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic groups, and C3~C 20 It is a group composed of aliphatic cyclic groups, and adjacent groups can combine with each other to form a ring. R1 and R2 can combine with each other to form a ring.

[0121] k, l, and n are integers from 0 to 4, and m is an integer from 0 to 6. Furthermore, when these are integers of 2 or higher, R... 8 R respectively 9 R respectively 10 They are the same or different.

[0122] R3 above is selected from C6 to C6. 20 aryl, fluorenyl, C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 20 heterocyclic group, C3~C 20 Aliphatic cyclic groups, C1-C 20 alkoxy groups, C6-C 20 aryloxy groups, C1-C 20 Alkyl groups, C2-C 20 alkenyl groups, and C2-C 20 The group is composed of acetyl groups.

[0123] Specifically, the compound represented by the above chemical formula 1 can be one of the following compounds, but is not limited to this.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] According to another aspect of the invention, the invention provides an organic electrical element comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by chemical formula 1.

[0134] According to another aspect of the present invention, the present invention provides an organic electrical element comprising an anode, a cathode, an organic layer located between the anode and the cathode, and a light efficiency improvement layer, wherein the light efficiency improvement layer is formed on one side of the anode and the cathode that is not in contact with the organic layer, and the organic layer or the light efficiency improvement layer may contain a compound represented by chemical formula 1.

[0135] The aforementioned organic layer may include at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. Preferably, the aforementioned compound may be included in the light-emitting auxiliary layer.

[0136] The aforementioned organic layer may include two or more stacks, which may include a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the aforementioned anode. The aforementioned organic layer may also include a charge generation layer formed between the aforementioned two or more stacks.

[0137] According to another aspect of the present invention, an electronic device is provided, comprising a display device and a control unit, wherein the display device comprises a compound represented by chemical formula 1, and the control unit is used to drive the display device.

[0138] The following examples illustrate the synthesis of compounds represented by chemical formula 1 and the preparation of organic electrical components according to the present invention, but the present invention is not limited to the following examples.

[0139] Synthesis example

[0140] Compounds represented by chemical formula 1 according to the present invention can be synthesized via the reaction pathway described in formula 1 below, but are not limited thereto.

[0141] <Reaction Formula 1> (Hal is I, Br, or Cl)

[0142]

[0143] Synthesis example of Sub1

[0144] Sub1 according to reaction formula 1 can be synthesized via the reaction pathway described in reaction formula 2 below, but is not limited thereto.

[0145] <Reaction 2>

[0146]

[0147] 1. Synthesis example of Sub1-1

[0148]

[0149] (1) Synthesis example of Sub1-1-b

[0150] 2-Iodobenzoic acid (50.0 g, 202 mmol), thiophenol (22.2 g, 202 mmol), KOH (56.6 g, 1008 mmol), and copper powder (1.3 g, 20.2 mmol) were placed in a round-bottom flask, and water (1.3 L) was added. The mixture was then refluxed for 12 hours. After the reaction was complete, 3 M HCl was added after cooling to room temperature until precipitation was complete. The precipitate was then wiped with water and dried to obtain 41.3 g of the product (yield: 89%).

[0151] (2) Example of the synthesis of Sub1-1-c

[0152] After adding 1.3 mL of H₂SO₄ to Sub₁₁₃ (41.3 g, 179 mmol), the mixture was refluxed until Sub₁₁₃ was completely dissolved. If Sub₁₁₃ was completely dissolved, the mixture was cooled to room temperature and then precipitated by adding ice water. The precipitate was then wiped with water, dried, and dissolved in CH₂Cl₂. Separation was then performed by silica gel column chromatography, followed by recrystallization to obtain 25.9 g of the product (yield: 68%).

[0153] (3) Example of the synthesis of Sub1-1-d

[0154] 2-Bromo-4'-chloro-1,1'-biphenyl (32.6 g, 122 mmol) was dissolved in THF (270 mL) under a nitrogen atmosphere and then cooled to -78 °C. n-BuLi (49 mL) was then slowly added dropwise while stirring the mixture for 30 minutes. A solution of Sub1-1-c (25.9 g, 122 mmol) dissolved in THF (140 mL) was then slowly added dropwise. The mixture was then stirred at -78 °C for 1 hour and slowly brought to room temperature. After the reaction was complete, the organic layer was extracted with ethyl acetate and water, dried over MgSO4, and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to give 40.1 g (yield: 82%) of the product.

[0155] (4) Example of the synthesis of Sub1-1-e

[0156] Sub1-1-d (40.1 g, 100 mmol), acetic acid (250 mL), and concentrated hydrochloric acid (40 mL) were placed in a round-bottom flask and stirred at 60–80 °C for 3 hours under a nitrogen atmosphere. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 31.8 g (yield: 83%) of the product.

[0157] (5) Synthesis example of Sub1-1

[0158] Sub1-1-e (31.8 g, 83.0 mmol) was dissolved in toluene (420 mL), and then dibenzo[b,d]thiophene-3-amine (16.5 g, 83.0 mmol), Pd2(dba)3 (2.28 g, 2.49 mmol), P(t-Bu)3 (1.01 g, 4.98 mmol), and NaOt-Bu (16.0 g, 166 mmol) were added. The mixture was stirred at 90 °C. After the reaction was complete, the product was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 32.6 g (yield: 72%) of the product.

[0159] 2. Synthesis example of Sub1-29

[0160]

[0161] (1) Synthesis example of Sub1-29-b

[0162] The product was synthesized using 3-chloro-2-iodobenzoic acid (20.0 g, 70.8 mmol), 3-(dibenzo[b,d]furan-3-yl)phenylthiohydroxy (19.6 g, 70.8 mmol), KOH (19.9 g, 354 mmol), and copper powder (0.45 g, 7.08 mmol) in the same manner as described in Sub1-1-b above, to obtain 25.6 g of the product (yield: 84%).

[0163] (2) Synthesis example of Sub1-29-c

[0164] Using Sub1-29-b (25.6 g, 59.4 mmol) and H2SO4 (420 mL), the product was synthesized in the same manner as that described above for Sub1-1-c, yielding 14.7 g of the product (yield: 60%).

[0165] (3) Synthesis example of Sub1-29-d

[0166] Using 2-bromo-1,1'-biphenyl (8.3 g, 35.6 mmol), n-BuLi (14 mL), and Sub1-29-c (14.7 g, 35.6 mmol), the product was synthesized in the same manner as that described above for Sub1-1-d, yielding 16.4 g of the product (yield: 81%).

[0167] (4) Synthesis example of Sub1-29-e

[0168] Using Sub1-29-d (16.4 g, 28.8 mmol), acetic acid (72 mL), and concentrated hydrochloric acid (12 mL), the product was synthesized using the same method as that described above for Sub1-1-e, to obtain 12.0 g of the product (yield: 76%).

[0169] (5) Synthesis example of Sub1-29

[0170] Using Sub1-29-e (12.0 g, 21.9 mmol), dibenzo[b, d]furan-3-amine (4.0 g, 21.9 mmol), Pd2(dba)3 (0.60 g, 0.66 mmol), P(t-Bu)3 (0.27 g, 1.31 mmol) and NaOt-Bu (4.2 g, 43.7 mmol), the product was synthesized using the same method as described above for Sub1-1, yielding 10.8 g of the product (yield: 71%).

[0171] 3. Synthesis examples of Sub1-48

[0172]

[0173] (1) Synthesis example of Sub1-48-b

[0174] The product was synthesized using 5-chloro-2-iodobenzoic acid (50.0 g, 177 mmol), phenol (33.3 g, 354 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (79.4 g, 531 mmol), pyridine (2.9 mL), copper powder (1.5 g, 23.0 mmol), and CuI (1.5 g, 7.97 mmol) in the same manner as described in Sub1-1-b above, to obtain 38.3 g of product (yield: 87%).

[0175] (2) Synthesis example of Sub1-48-c

[0176] Using Sub1-48-b (38.3 g, 154 mmol) and H2SO4 (1.1 L), the product was synthesized in the same manner as that described above for Sub1-1-c, yielding 23.1 g of the product (yield: 65%).

[0177] (3) Synthesis example of Sub1-48-d

[0178] The product was synthesized using 2-bromo-1,1'-biphenyl (23.3 g, 100 mmol), n-BuLi (40 mL), and Sub1-48-c (23.1 g, 100 mmol) in the same manner as the synthesis of Sub1-1-d described above, to obtain 32.8 g of the product (yield: 85%).

[0179] (4) Example of the synthesis of Sub1-48-e

[0180] Using Sub1-48-d (32.8 g, 85.1 mmol), acetic acid (210 mL), and concentrated hydrochloric acid (35 mL), the product was synthesized using the same method as that described above for Sub1-1-e, yielding 28.4 g of the product (yield: 91%).

[0181] (5) Synthesis example of Sub1-48

[0182] Using Sub1-48-e (28.4 g, 77.4 mmol), dibenzo[b,d]furan-1-amine (14.2 g, 77.4 mmol), Pd2(dba)3 (2.13 g, 2.32 mmol), P(t-Bu)3 (0.94 g, 4.65 mmol) and NaOt-Bu (14.9 g, 155 mmol), the product was synthesized using the same method as described above for Sub1-1, yielding 29.8 g of the product (yield: 75%).

[0183] 4. Synthesis example of Sub1-67

[0184]

[0185] (1) Synthesis example of Sub1-67-b

[0186] 2-Iodobenzoic acid (50.0 g, 202 mmol), phenol (37.9 g, 403 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (90.4 g, 605 mmol), pyridine (3.2 mL), copper powder (1.7 g, 26.2 mmol), and CuI (1.7 g, 9.07 mmol) were placed in a round-bottom flask, and DMF (1.6 L) was added. The mixture was then refluxed for 3 hours. After the reaction was complete, 3 M HCl was added after cooling to room temperature until precipitation was complete. The precipitate was then wiped with water and dried to obtain 41.8 g of the product (yield: 86%).

[0187] (2) Synthesis example of Sub1-67-c

[0188] Using Sub1-67-b (41.8 g, 195 mmol) and H2SO4 (14 L), the product was synthesized in the same manner as that described above for Sub1-1-c, yielding 26.4 g of the product (yield: 69%).

[0189] (3) Synthesis example of Sub1-67-d

[0190] The product was synthesized using 2-bromo-2'-chloro-1,1'-biphenyl (36.0 g, 135 mmol), n-BuLi (54 mL), and Sub1-67-c (26.4 g, 135 mmol) in the same manner as the synthesis of Sub1-1-d described above, to obtain 45.1 g of the product (yield: 87%).

[0191] (4) Synthesis example of Sub1-67-e

[0192] Using Sub1-67-d (45.1 g, 117 mmol), acetic acid (290 mL), and concentrated hydrochloric acid (50 mL), the product was synthesized in the same manner as that described above for Sub1-1-e, yielding 40.4 g of the product (yield: 94%).

[0193] (5) Synthesis example of Sub1-67

[0194] Using Sub1-67-e (40.4 g, 110 mmol), dibenzo[b,d]furan-2-amine (20.2 g, 110 mmol), Pd2(dba)3 (3.03 g, 3.30 mmol), P(t-Bu)3 (1.34 g, 6.61 mmol) and NaOt-Bu (21.2 g, 220 mmol), the product was synthesized using the same method as described above for Sub1-1, yielding 38.4 g of the product (yield: 68%).

[0195] The compounds belonging to Sub1 can be the same as those listed below, but are not limited to them. The FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are shown in Table 1.

[0196]

[0197]

[0198]

[0199] [Table 1]

[0200]

[0201]

[0202]

[0203] Synthesis example of the final product

[0204] Synthesis example 1.1-1

[0205]

[0206] (1) Example of synthesis of Inter-1

[0207] 1-Bromo-4-chlorobenzene (7.66 g, 40 mmol) was dissolved in toluene (150 mL), followed by the addition of diphenylamine (7.45 g, 44.01 mmol), Pd₂(dba)₃ (1.8 g, 2 mmol), P(t-Bu)₃ (0.8 g, 4 mmol), and NaOt-Bu (11.5 g, 120 mmol), and the mixture was stirred at 60 °C. After the reaction was complete, the mixture was extracted with CH₂Cl₂ and water, and the organic layer was dried over MgSO₄ and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 9.9 g (yield: 89%) of the product.

[0208] (2) Synthesis example of 1-1

[0209] Inter-1 (5.6 g, 20 mmol) was dissolved in toluene (25 mL), and Sub1-65 (11.3 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol) were added, followed by reflux. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated by silica gel column chromatography and recrystallized to obtain 12 g (yield: 79%) of the product.

[0210] Synthesis examples 2.1-29

[0211]

[0212] (1) Synthesis example of Inter-29

[0213] The product was synthesized using 1-bromo-4-chlorobenzene (7.6 g, 40 mmol), N-phenyldibenzo[b, d]furan-1-amine (11.4 g, 44 mmol), Pd2(dba)3 (1.8 g, 2 mmol), P(t-Bu)3 (0.8 g, 4 mmol) and NaOt-Bu (11.5 g, 120 mmol) in the same manner as the synthesis of Inter-1 described above, to obtain 22.4 g of product (yield: 74%).

[0214] (2) Synthesis examples of 1-29

[0215] Using Inter-29 (5.6 g, 20 mmol), Sub1-49 (11.3 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol), the product was synthesized using the same method as described in section 1-1 above, yielding 14.2 g of the product (yield: 84%).

[0216] Synthesis examples 3.1-56

[0217]

[0218] (1) Example of Inter-56 synthesis

[0219] The product was synthesized using 1-bromo-3-chlorobenzene (7.6 g, 40 mmol), diphenylamine (7.4 g, 44 mmol), Pd2(dba)3 (1.8 g, 2 mmol), P(t-Bu)3 (0.8 g, 4 mmol) and NaOt-Bu (11.5 g, 120 mmol) in the same manner as the synthesis of Inter-1 described above, to obtain 4.9 g of product (yield: 87%).

[0220] (2) Synthesis examples of 1-56

[0221] Using Inter-56 (5.6 g, 20 mmol), Sub1-117 (12 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol), the product was synthesized using the same method as described in section 1-1 above, yielding 11.7 g of the product (yield: 74%).

[0222] Synthesis example 4.1-80

[0223]

[0224] (1) Example of Inter-80 synthesis

[0225] The product was synthesized using 1-bromo-3-chlorobenzene (7.6 g, 40 mmol), diphenylamine (7.4 g, 44 mmol), Pd2(dba)3 (1.8 g, 2 mmol), P(t-Bu)3 (0.8 g, 4 mmol) and NaOt-Bu (11.5 g, 120 mmol) in the same manner as the synthesis of Inter-1 described above, to obtain 4.9 g of product (yield: 87%).

[0226] (2) Synthesis examples of 1-80

[0227] Using Inter-80 (5.6 g, 20 mmol), Sub1-93 (14 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol), the product was synthesized using the same method as described in section 1-1 above, yielding 14.3 g of the product (yield: 81%).

[0228] Synthesis examples 5.1-95

[0229]

[0230] (1) Example of Inter-95 synthesis

[0231] The product was synthesized using 1-bromo-3-chlorobenzene (7.6 g, 40 mmol), N-phenylnaphthyl-1-amine (9.7 g, 44 mmol), Pd2(dba)3 (1.8 g, 2 mmol), P(t-Bu)3 (0.8 g, 4 mmol) and NaOt-Bu (11.5 g, 120 mmol) in the same manner as the synthesis of Inter-1 described above, to obtain 11.2 g of product (yield: 85%).

[0232] (2) Synthesis examples of 1-95

[0233] Using Inter-95 (6.6 g, 20 mmol), Sub1-126 (12 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol), the product was synthesized using the same method as described in section 1-1 above, to obtain 12 g of product (yield: 72%).

[0234] Synthesis examples 6.1-113

[0235]

[0236] The product was synthesized using 4,4'-dibromo-1,1'-biphenyl (3.1 g, 10 mmol), Sub1-63 (11.3 g, 22 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), P(t-Bu)3 (0.2 g, 1 mmol) and NaOt-Bu (2.9 g, 30 mmol) in the same manner as described in section 1-1 above, to obtain 12 g of product (yield: 72%).

[0237] Synthesis examples 7.1-133

[0238]

[0239] (1) Synthesis example of Inter-133

[0240] The product was synthesized using 1-bromo-3-chlorodibenzo[b,d]furan (11.3 g, 40 mmol), diphenylamine (7.4 g, 44 mmol), Pd2(dba)3 (1.8 g, 2 mmol), P(t-Bu)3 (0.8 g, 4 mmol), and NaOt-Bu (11.5 g, 120 mmol) in the same manner as the synthesis of Inter-1 described above, to obtain 11.7 g of product (yield: 79%).

[0241] (2) Synthesis example of 1-133

[0242] The product was synthesized using Inter-133 (7.4 g, 20 mmol), Sub1-48 (12 g, 22 mmol), Pd2(dba)3 (0.9 g, 1 mmol), P(t-Bu)3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol) in the same manner as described in section 1-1 above, to obtain 13.9 g of the product (yield: 82%).

[0243] The FD-MS values ​​of compounds 1-1 to 1-180 of the present invention prepared according to the synthesis examples described above are as shown in Table 2 below.

[0244] [Table 2]

[0245]

[0246]

[0247]

[0248]

[0249] Evaluation of the manufacture of organic electrical components

[0250] [Example 1] Green organic electroluminescent element (light-emitting auxiliary layer)

[0251] After forming a hole injection layer with a thickness of 60 nm by vacuum deposition of a 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as “2-TNATA”) film on an ITO layer (anode) formed on a glass substrate, a hole transport layer is formed by vacuum deposition of a 60 nm-thick N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as “NPB”) film on the hole injection layer.

[0252] Subsequently, compound 1-1 of the present invention was vacuum-deposited on the hole transport layer to form a light-emitting auxiliary layer with a thickness of 20 nm. 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") was used as the host material on the light-emitting auxiliary layer, and tris(2-phenylpyridine)iridium (hereinafter referred to as "Ir(ppy)3") was used as the dopant material at a weight ratio of 95:5. The light-emitting layer was vacuum-deposited to a thickness of 30 nm.

[0253] Next, a hole blocking layer is formed on the light-emitting layer by vacuum deposition of (1,1'-biphenyl-4-hydroxy)bis(2-methyl-8-hydroxyquinoline)aluminum (hereinafter referred to as "BAlq") with a thickness of 10 nm, and an electron transport layer is formed on the hole blocking layer by vacuum deposition of tri(8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq3") with a thickness of 40 nm.

[0254] Then, LiF is deposited at a thickness of 0.2 nm for the electron transport layer, followed by aluminum deposition at a thickness of 150 nm to form the cathode, thus fabricating an organic light-emitting element.

[0255] [Example 2] to [Example 20]

[0256] The material used as the light-emitting auxiliary layer was the compound of the present invention listed in Table 3 below, which was used instead of compound 1-1 of the present invention. Otherwise, the organic electroluminescent element was prepared in the same manner as in Example 1 above.

[0257] [Comparative Example 1]

[0258] Except for the absence of a light-emitting auxiliary layer, the organic electroluminescent element was fabricated using the same method as in Example 1 described above.

[0259] Comparative Examples 2 to 4

[0260] Organic electroluminescent elements were fabricated using the same method as in Example 1 above, except that one of the comparative compounds A to C was used as the light-emitting auxiliary layer.

[0261]

[0262]

[0263] A forward bias DC voltage was applied to the organic electroluminescent elements prepared according to Examples 1 to 20 and Comparative Examples 1 to 4 of the present invention, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. The results were obtained at 5000 cd / m². 2 In the reference brightness test, the T95 lifetime was measured using a lifetime measurement device manufactured by MC Science, a South Korean company. The measurement results are shown in Table 3 below.

[0264] [Table 3]

[0265]

[0266]

[0267] As can be seen from Table 3 above, compared with the case where no light-emitting auxiliary layer is formed (Comparative Example 1) or one of the comparative compounds A to C is used (Comparative Examples 2 to 4), when the compound represented by Chemical Formula 1 of the present invention is used as the light-emitting auxiliary layer material, the driving voltage is significantly reduced and the luminous efficiency and lifetime are significantly improved.

[0268] Comparative compounds A through C are similar to the compounds of the present invention in terms of skeleton, but differ in the types of substituents that replace amino groups.

[0269] The compounds of the present invention, while substituting the same amino group with a substituent comprising chemical formula A-1 or A-2, also substitute heterocycles comprising parts of dibenzofuran, dibenzothiophene, carbazole, etc., which have high thermal stability and cavitation properties. Conversely, comparative compounds A to C are similar to the present invention in that the amino group is substituted with a substituent represented by chemical formula A-1 or A-2 (spiro[fluorene-9,9'-xanthine]), but differ in that the remaining substituents of the same amino group are phenyl (comparative compound A) or fluorenyl (comparative compounds B and C).

[0270] Due to these differences in substituents, the compound of the present invention significantly improves the characteristics of the element compared to the comparative compound. This is because with the substitution of the amine group with a heterocyclic group (dibenzofuran, dibenzothiophene, carbazole, etc.) that has high thermal stability and hole-trapping properties, there is relatively more space to trap holes, thereby increasing the charge balance within the light-emitting layer.

[0271] Therefore, it can be seen that even compounds with similar structures will have different physical properties depending on the type of substituents, such as hole characteristics, light efficiency characteristics, hole injection and migration characteristics, and such differences will affect the characteristics of the device.

[0272] The above description is merely illustrative. Those skilled in the art can make various modifications without departing from the essential characteristics of the invention. Therefore, the embodiments disclosed in this specification are not intended to limit the invention, but rather to illustrate it. The scope of the invention is not limited by such embodiments. The scope of protection of this invention should be interpreted according to the scope of the claims, and all technologies within the same scope should be interpreted as included within the scope of the invention.

[0273] Cross-referencing of related patent applications

[0274] This patent application claims priority to U.S. Patent No. 10-2020-0096221, filed in Korea on July 31, 2020, pursuant to Sections 119 to 121 and 365 of the United States Patent Act (35 U.S.SC §119 to 121, §365), the entire contents of which are incorporated herein by reference. Furthermore, if this patent application claims priority in any other country outside the United States on the same grounds, the entire contents of that country are incorporated herein by reference.

Claims

1. A compound represented by the following chemical formula 1, wherein, <Chemical Formula 1> In the above chemical formula 1, Ar 1 It is either chemical formula A-1 or chemical formula A-2. Ar 2 and Ar 3 Choose independently from C6 to C6. 20 The group consisting of aryl; pyridyl; pyrimidinyl; pyrazinyl; pyridazinyl; dibenzofuranyl; and dibenzothiopheneyl. X 1 For O or S, X 2 For O or S, R 1 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C1-C2 30 Alkyl groups; and C1-C 30 The group consists of alkoxy groups, and adjacent groups can combine with each other to form a benzene ring. R 2 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C6-C 20 aryl; C1~C 30 Alkyl groups; and C1-C 30 The group consisting of alkoxy groups, R 3 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C6-C 20 aryl; dibenzothiophene; dibenzofuranyl; C1-C 30 Alkyl groups; and C1-C 30 The group consists of alkoxy groups, and adjacent groups can combine with each other to form a 2-condensation ring of benzothiophene or benzofuran, ultimately forming a 3-condensation ring of dibenzothiophene or dibenzofuran. R 4 To R 7 The elements are independently selected from hydrogen, deuterium, halogen, and C1–C2. 30 Alkyl groups; and C1-C 30 The group consisting of alkoxy groups, a, c, d, e, f, and g are integers from 0 to 4, and b, e', and g' are integers from 0 to 3. Furthermore, when these are integers of 2 or higher, R... 1 R respectively 2 R respectively 3 R respectively 4 R respectively 5 R respectively 6 R respectively 7 Whether they are the same or different, L 1 To L 4 Independently selectable single bonds; and C6~C 30 The group composed of aryl groups. The rings formed by the combination of the above-mentioned aryl, arylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzofuranyl, dibenzothiopheneyl, alkyl, alkoxy, and adjacent groups can be selected from deuterium, halogen, cyano, nitro, C1-C1 groups, respectively. 20 alkoxy groups, C1-C 20 Alkyl groups, and C6-C 20 One or more substituents in the group consisting of aryl groups are further substituted.

2. The compound according to claim 1, wherein, Ar 2 and Ar 3 The groups are independently selected from the group consisting of phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzofuranyl, and dibenzothiophene, wherein the aforementioned phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzofuranyl, and dibenzothiophene are selected from deuterium, halogen, cyano, nitro, C1-C1, C2-C3, C4-C4, C5-C6 ... 20 alkoxy groups, C1-C 20 Alkyl groups, and C6-C 20 One or more substituents in the group consisting of aryl groups are further substituted.

3. The compound according to claim 1, wherein, The above chemical formula 1 is represented by one of the following chemical formulas 1-1 to 1-6. In the above chemical formulas 1-1 to 1-6, X 1 X 2 L 1 ~L 4 Ar 2 Ar 3 R 1 ~R 7 a to g are defined in the same way as in claim 1, and e' and g' are integers from 0 to 3 respectively.

4. A compound represented by one of the following chemical formulas 1-7 to 1-18, In the above chemical formulas 1-7 to 1-18, X 1 X 2 L 1 ~L 4 Ar 2 Ar 3 R 1 R 2 R 4 ~R 7 a to g are defined as in claim 1, and e' and g' are integers from 0 to 3. V 1 and V 2 They are independently single bonds, O, S, C(R1)(R2) or N(R3), and V 1 and V 2 Except for cases where all keys are single keys. The above R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C2. 20 alkoxy groups, C1-C 20 Alkyl groups, and C6-C 20 The group composed of aryl groups. R3 above refers to C1 to C 20 Alkyl groups.

5. A compound represented by the following chemical formula 1, wherein, <Chemical Formula 1> In the above chemical formula 1, Ar 1 It is either chemical formula A-1 or chemical formula A-2. X 1 For O or S, X 2 For O or S, R 1 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C1-C2 30 Alkyl groups; and C1-C 30 The group consists of alkoxy groups, and adjacent groups can combine with each other to form a benzene ring. R 2 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C6-C 20 aryl; C1~C 30 Alkyl groups; and C1-C 30 The group consisting of alkoxy groups, R 3 Choose from: hydrogen; deuterium; halogen; cyano; nitro; C6-C 20 aryl; dibenzothiophene; dibenzofuranyl; C1-C 30 Alkyl groups; and C1-C 30 The group consists of alkoxy groups, and adjacent groups can combine with each other to form a 2-condensation ring of benzothiophene or benzofuran, ultimately forming a 3-condensation ring of dibenzothiophene or dibenzofuran. R 4 To R 7 The elements are independently selected from hydrogen, deuterium, halogen, and C1–C2. 30 Alkyl groups; and C1-C 30 The group consisting of alkoxy groups, a, c, d, e, f, and g are integers from 0 to 4, and b, e', and g' are integers from 0 to 3. Furthermore, when these are integers of 2 or higher, R... 1 R respectively 2 R respectively 3 R respectively 4 R respectively 5 R respectively 6 R respectively 7 Whether they are the same or different, L 1 To L 4 Independently selectable single bonds; and C6~C 30 The group composed of aryl groups. The rings formed by the combination of the above-mentioned aryl, arylene, alkyl, alkoxy, and adjacent groups can be selected from deuterium, halogen, cyano, nitro, C1-C1 groups, respectively. 20 alkoxy groups, C1-C 20 Alkyl groups, and C6-C 20 One or more substituents in the group consisting of aryl groups are further substituted; Ar 2 and Ar 3 At least one of the following is selected from the group consisting of chemical formulas 2-1 to 2-6: In the above chemical formulas 2-1 to 2-6, X 4 and X 5 They are independently O, S, C(R1)(R2) or N(R3). The above R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C2. 20 alkoxy groups, and C1-C 20 The group consisting of alkyl groups, The above R 8 R 9 and R 10 The groups are independently selected from hydrogen, deuterium, halogen, cyano, nitro, and C1-C2. 20 alkoxy groups, C1-C 20 Alkyl groups, and C6-C 20 The group composed of aryl groups. k, l, and n are integers from 0 to 4, and m is an integer from 0 to 6. Furthermore, when these are integers of 2 or higher, R... 8 R respectively 9 R respectively 10 Whether they are the same or different, R3 above refers to C1 to C 20 Alkyl groups.

6. A compound that is one of the following:

7. An organic electrical component, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein, The aforementioned organic layer includes a light-emitting auxiliary layer, which comprises a compound according to any one of claims 1-6.

8. The organic electrical component according to claim 7, wherein, It also includes a light efficiency improvement layer, which is formed on the side of the first electrode and the second electrode that is not in contact with the organic layer.

9. The organic electrical component according to claim 7, wherein, The light-emitting layer of the aforementioned organic layer includes the aforementioned compound.

10. The organic electrical component according to claim 8, wherein, The aforementioned light efficiency improvement layer includes the aforementioned compound.

11. The organic electrical component according to claim 7, wherein, The aforementioned organic layer comprises two or more stacks, including a hole transport layer, a light-emitting layer, and an electron transport layer formed sequentially on the aforementioned first electrode.

12. The organic electrical component according to claim 11, wherein, The aforementioned organic layer also includes a charge generation layer formed between the two or more stacks.

13. An electronic device, wherein, include: The display device includes the organic electrical component according to claim 7; as well as The control unit is used to drive the aforementioned display device.

14. The electronic device according to claim 13, wherein, The aforementioned organic electrical components are selected from the group consisting of organic light-emitting elements, organic solar cells, organic photosensitive elements, organic transistors, monochrome lighting elements, and quantum dot display elements.

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